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Uncovering the Formation and Selection of Benzylmalonyl-CoA from the Biosynthesis of Splenocin and Enterocin Reveals a Versatile Way to Introduce Amino Acids into Polyketide Carbon Scaffolds
Alternative Titlesplenocin和促肠活动素生物合成中苯甲基丙二酰CoA的形成和选择机制的揭示展现了一种通用的氨基酸引入聚酮化合物碳骨架的方式
Chang CC(常晨晨)1; Huang R(黄荣)1; Yan Y(闫岩)1; Ma HM(马宏敏)1; Dai Z(戴政)1; Zhang BY(张本印)1; Deng ZX(邓子新)1; Liu W(刘文)1; Ju XD(瞿旭东)1
2015
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:12Pages:4183-4190
AbstractSelective modification of carbon scaffolds via biosynthetic engineering is important for polyketide structural diversification. Yet, this scope is currently restricted to simple aliphatic groups due to (1) limited variety of CoA-linked extender units, which lack aromatic structures and chemical reactivity, and (2) narrow acyltransferase (AT) specificity, which is limited to aliphatic CoA-linked extender units. In this report, we uncovered and characterized the first aromatic CoA-linked extender unit benzylmalonyl-CoA from the biosynthetic pathways of splenocin and enterocin in Streptomyces sp. CNQ431. Its synthesis employs a deamination/reductive carboxylation strategy to convert phenylalanine into benzylmalonyl-CoA, providing a link between amino acid and CoA-linked extender unit synthesis. By characterization of its selection, we further validated that AT domains of splenocin, and antimycin polyketide synthases are able to select this extender unit to introduce the phenyl group into their dilactone scaffolds. The biosynthetic machinery involved in the formation of this extender unit is highly versatile and can be potentially tailored for tyrosine, histidine and aspartic acid. The disclosed aromatic extender unit, amino acid-oriented synthetic pathway, and aromatic-selective AT domains provides a systematic breakthrough toward current knowledge of polyketide extender unit formation and selection, and also opens a route for further engineering of polyketide carbon scaffolds using amino acids.
Subtype论文
Subject Area生命有机化学
DOI10.1021/jacs.5b00728
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000352244800033
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39497
Collection生命有机化学国家重点实验室
Corresponding AuthorJu XD(瞿旭东)
Affiliation1.武汉大学
2.中科院上海有机化学研究所, 生命有机化学国家重点实验室
Recommended Citation
GB/T 7714
Chang CC,Huang R,Yan Y,et al. Uncovering the Formation and Selection of Benzylmalonyl-CoA from the Biosynthesis of Splenocin and Enterocin Reveals a Versatile Way to Introduce Amino Acids into Polyketide Carbon Scaffolds[J]. J. Am. Chem. Soc.,2015,137(12):4183-4190.
APA 常晨晨.,黄荣.,闫岩.,马宏敏.,戴政.,...&瞿旭东.(2015).Uncovering the Formation and Selection of Benzylmalonyl-CoA from the Biosynthesis of Splenocin and Enterocin Reveals a Versatile Way to Introduce Amino Acids into Polyketide Carbon Scaffolds.J. Am. Chem. Soc.,137(12),4183-4190.
MLA 常晨晨,et al."Uncovering the Formation and Selection of Benzylmalonyl-CoA from the Biosynthesis of Splenocin and Enterocin Reveals a Versatile Way to Introduce Amino Acids into Polyketide Carbon Scaffolds".J. Am. Chem. Soc. 137.12(2015):4183-4190.
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